Sadly, still the same problem. The funny thing is I have the same version of Outlook working in parallel on my MacBook Air and it is working fine. It is only the iMac which is causing me problems and only Outlook.

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Hold down Shift key on your Keyboard and open Outlook. Does it starts Outlook ?

Open Documents, and then open Microsoft User Data. Move the Office 2011 Identities folder to the desktop. Make sure you are moving it, not copying it to desktop. There won't be any Identities folder in Office 2011 folder when you move it. Open Outlook. Does that works ?

Good news! I successfully loaded Outlook on the administrator account. Should I follow the same process on my main login....delete the old version and reinstall a new copy? If yes, can I protect all my old emails so I don't lose them?